π π* * Transition in Alkenes Transitions between electron energy states Ultraviolet-Visible (UV-VIS) Spectroscopy
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1 Transitions between electron energy states Ultraviolet-Visible (UV-VIS) Spectroscopy Gives information about conjugated π electron systems ΔE = hν gaps between electron energy levels are greater than those between vibrational levels gap corresponds to wavelengths between 200 and 800 nm onventions in UV-VIS UV and Visible light cause only two kinds of electronic transitions X-axis is wavelength in nm (high energy at left, low energy at right) λ max is the wavelength of maximum absorption and is related to electronic makeup of molecule especially π electron system Y axis is a measure of absorption of electromagnetic radiation expressed as Absorbance or molar absorptivity (ε) Only organic compounds with π electrons can absorb energy in the UV/Visible region A visible spectrum is obtained if visible light is absorbed A UV spectrum is obtained if UV light is absorbed π π* * Transition in cis,trans-1,3-cyclooctadiene cyclooctadiene π π* * Transition in Alkenes LUMO OMO ψ 4 ψ 3 ψ 2 ΔE = hν ψ 4 ψ 3 ψ 2 OMO-LUMO energy gap is affected by substituents on double bond as OMO-LUMO energy difference decreases (smaller ΔE), λ max shifts to longer wavelengths ψ 1 ψ 1 Most stable π-electron configuration π-electron configuration of excited state 1
2 Substituent Effects A chromophore is the part of a molecule which absorbs UV or visible light Methyl groups on double bond cause λ max to shift to longer wavelengths 3 3 λ max 170 nm λ max 188 nm Effect of onjugation on λ max Substituent Effects O 3 2 Extending conjugation has a larger effect on λ max ; shift is again to longer wavelengths UV Spectrum: ()-carvone 236 nm λ max 170 nm λ max 217 nm Wavelength (nm) Series1 What is carvone s λ max? 2
3 The Beer Lambert Law UV Spectrum of cis,trans-1,3-cyclooctadiene cyclooctadiene A = clε A = log(i / I 0 ) c = concentration of substance in solution l = length of the cell in cm ε = molar absorptivity The molar absorptivity of a compound is a constant that is characteristic of the compound at a particular wavelength 2000 Molar absorptivity (ε) Wavelength, nm λ max max 230 nm ε max Substituent Effects λ max 217 nm (conjugated diene) Both the λ max and ε increase as the number of conjugated double bonds increases λ max 263 nm conjugated triene plus two methyl groups 3 An auxochrome is a substituent in a chromphore that alters the λ max and the intensity of the absorption Uses of UV/Vis Spectroscopy Measure the rates of a reaction Determine the pk a of a compound Estimate the nucleotide composition of DNA 3
4 The Visible Spectrum and olor Vision Biological / Physiological response to light stimuli 4
5 The Eye and Vision The Eye and its Neurological Wiring Vision: Receptive Field (RF) Definition: the area of the retina (or visual field) in which light signals evoke responses It s a property of the cell, not a cell or a part of the cell It depends largely on the synaptic inputs to the cell and to some degree the biophysical property of the cell itself Visual pathway from retina to V1 Projection from retina to LGN fixation point fovea Nasal RG: axons crossover, project to contralateral LGN Temporal RG: axons stay on the same side (ipsilateral) Left visual field: right LGN, right V1 Right visual field: left LGN, left V1 Optical imaging of orientation map 5
6 Retinotopic map The Retina & Photoreceptive ells neighboring cells have neighboring RF retinotopic map is true in the retina, LGN and V1, but it gets fuzzy as you move on to higher visual areas c b a Project orderly to LGN and V1 a b c object retina Different cells in the retina light The Basic Retinal ircuit Back of eye 6. Pigment cells 1. Receptor ells (Graded potential) (input) 2. Bipolar ells (Graded potential) 3. Ganglion ells (action potential) (Output) Stru cture of th e eye 4. orozontal ells (Graded potential) 5. Amacrine ells (Graded/action potential) Fovea: high spatial resolution Periphery: low spatial resolution Front of eye 2 Direct pathway: Photo receptor Bipolar RG Indirect pathway Photoreceptor - On bipolar Photoreceptor Off bipolar orizontal cell - Photoreceptor On RG Off RG : excitatory synapse, preserve response direction -: inhibitory synapse, flip response direction Indirect pathway mediated by horizontal is responsible to the RF surround There are other indirect pathway mediated by amacrine cells Direct pathway is responsible to the RF center 6
7 Summary of retinal circuit Direct pathway - On bipolar On RG Photoreceptor Off bipolar Off RG Indirect pathway - Photoreceptor orizontal cell Pathways mediated by amacrine cells Photoreceptor The Nobel Prize in Physiology or Medicine 1981: Roger W.Sperry: for his discoveries concerning the functional specialization of the cerebral hemispheres David. ubel & Torsten N. Wiesel: for their discoveries concerning information processing in the visual system in Vision an diet affect sight?...it might depend on what you re looking at. olor vision vs. B&W: Rods vs. ones The Photochemical Process Lycopenes arotenes Retinol / Retinal umans only see in B&W at night, but some animals like the nocturnal hawkmoth see color. Nature, , 2002 Lycopene orange-red pigment in tomatoes λ max 505 nm Lycopene Lycopene Beta arotene "Pro vitamin A" Beta arotene "Pro vitamin A" O O O O 7
8 Lycopene Lycopene Beta arotene "Pro vitamin A" Beta arotene "Pro vitamin A" O O O O is-trans Isomerization & Vision Lycopene Beta arotene "Pro vitamin A" O O B&W hemistry Step One: Oxidation B&W hemistry Step Two: Trans -> is Isomerization O O O O 8
9 B&W hemistry Step Three: ooked on Opsin B&W hemistry Step Four: Flash O N 2 Opsin N ~ 5 photons ~ 3 picosec N N B&W hemistry Step Five: Repeat Process N O N 2 Opsin are natural products that form from a pyrophosphate and are structurally related to isoprene Vision exercise Isoprene (2-methyl-1,3-butadiene) O O O P O P O O Isopentenyl pyrophosphate O Isoprene 9
10 The Isoprene Unit An isoprene unit is the carbon skeleton of isoprene (ignoring the double bonds) The Isoprene Unit The isoprene units are joined "head-totail." head tail Two isoprene units: tail head Isoprene Links eads or Tails? ommon arbon Backbone 10
11 lassification of Representative Monoterpenes lass Number of carbon atoms Monoterpene 10 Sesquiterpene 15 Diterpene 20 Sesterpene 25 Triterpene 30 Tetraterpene 40 α-phellandrene (eucalyptus) Menthol (peppermint) O O itral (lemon grass) Representative Monoterpenes Representative Monoterpenes O O α-phellandrene (eucalyptus) Menthol (peppermint) itral (lemon grass) α-phellandrene (eucalyptus) Menthol (peppermint) itral (lemon grass) Representative Sesquiterpenes Representative Sesquiterpenes α-selinene (celery) α-selinene (celery) 11
12 Representative Sesquiterpenes Representative Diterpenes O α-selinene (celery) Representative Diterpenes Representative Diterpenes O ommon O O Limonene 2 Linalool O Nerol O O Geraniol O O Terpineol O 2 12
13 Limonene 2 13
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